Headless Horseman Hussle 2026 — Sleepy Hollow, IL
The Headless Horseman Hustle takes place at 898 Glen Oak Dr in Sleepy Hollow, Illinois on September 20, 2026. This running event features a 5K distance and starts at 9:00 AM. The entry fee is $30.00. Whether you're training through the fall season or looking for a local race to test your fitness, this 5K offers a straightforward option for runners in the area. Plan your travel accordingly if you're coming from out of town, and arrive early to handle registration before the 9:00 AM start.
Course & Travel Notes
The Headless Horseman Hussle takes place on September 20, 2026, in Sleepy Hollow, Illinois, with the race starting at 9:00 AM—giving you plenty of time after sunrise at 6:38 AM to prepare. The venue sits at 755 feet elevation, which is relatively modest for course planning. You can fly into Dupage Airport (DPA), located 13 miles from the race site, and expect typical early fall weather with highs around 76°F and lows near 53°F, though there's a 30% chance of measurable rain on any given day that time of year.
Hotels Near This Race
Find accommodation close to the start line in Sleepy Hollow, IL. Sorted by distance from the race venue. Book early — race weekend hotels fill fast.
Headless Horseman Hussle 2026 — Sleepy Hollow, IL
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Race Travel Insurance
Don't forget travel insurance for September 20.
You've trained for months and booked a trip to Sleepy Hollow, IL. A pre-race injury, a delayed flight, or a family emergency can derail the whole thing. Travel insurance can help cover your race entry fee, hotel, and flights if you can't make it, and may cover medical costs if something goes wrong on the course. Plans typically only run 5-7% of your total trip cost — and running events are covered under standard plans with no additional coverage needed.
- Trip cancellation up to 100% of prepaid costs
- Running events covered under standard plans — no add-ons needed
- Trip interruption up to 150% of non-refundable costs
- Emergency medical up to $250,000
- Cancel For Any Reason add-on available
- 24/7 real-time support
Affiliate links — we may earn a commission at no cost to you. Coverage terms vary by state and plan. Review policy details before purchase.
Frequently Asked Questions
When is Headless Horseman Hussle 2026 — Sleepy Hollow, IL?
Headless Horseman Hussle 2026 — Sleepy Hollow, IL takes place on September 20, 2026. The race is held in Sleepy Hollow, Illinois.
Where is Headless Horseman Hussle 2026 — Sleepy Hollow, IL held?
Headless Horseman Hussle 2026 — Sleepy Hollow, IL is held at 898 Glen Oak Dr in Sleepy Hollow, Illinois.
Where can I find hotels near Headless Horseman Hussle 2026 — Sleepy Hollow, IL?
RaceHotelFinder shows hotels sorted by distance from the race venue in Sleepy Hollow. Use the map or list view on this page to compare options and book race weekend accommodation.